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Research Summary: While previous organizational impression management (OIM) research focuses on highlighting firms in a favorable light, we explore CEOs' use of "strategic negativity" to manage expectations. We draw on OIM's psychological roots to predict that despite pressure to "be positive," when CEOs perceive stakeholders are motivated to raise their expectations and have an opportunity to do so, CEOs strategically use negativity to counteract this anticipated expectation increase. We test our predictions on 7330 quarterly earnings calls from 370 publicly traded firms (2008–2019), examining how the "motive" of a positive material earnings surprise and "opportunity" of a new fiscal year jointly increase CEO negativity in prepared remarks. We elaborate the wide applicability of strategic negativity, the "other side" of the OIM phenomenon. Managerial Summary: In contrast to the prevailing view that CEOs usually "positively spin" the firm's situation to stakeholders, we investigate how CEOs strategically use negativity to counteract stakeholder optimism, provided CEOs perceive expectations are likely to rocket upward. We argue that positive news represents a "motive" and a chance to reflect represents an "opportunity," and that together they risk raising expectations. Analyzing 7330 quarterly earnings calls of 370 companies (2008–2019), we specifically examined how both (1) a positive earnings surprise and (2) a new fiscal year force CEOs out of their positivity comfort zone and encourage them to be strategically negative in earnings call remarks, to try to lower stakeholder expectations. Our results support this view and pave the way for future research. [ABSTRACT FROM AUTHOR]